Limited attention has been directed toward examining post-adoption stages of the information system life cycle. In particular, the final stages of this life cycle have been largely ignored despite the fact that most systems eventually reach the end of their useful life. This oversight is somewhat surprising given that end-of-life decisions can have significant implications for user effectiveness, the value extracted from IS investments, and organizational performance. Given this apparent gap, a multi-method empirical study was undertaken to improve our understanding of organizational level information system discontinuance. Research commenced with the development of a broad theoretical framework consistent with the technology—organization—environment (TOE) paradigm. The resulting framework was then used to guide a series of semi-structured interviews with organizational decision makers in an effort to inductively identify salient influences on the formation of IS discontinuance intentions. A set of research hypotheses were formulated based on the understanding obtained during these interviews and subsequently tested via a random survey, of senior IS decision makers at U.S. and Canadian organizations. Data obtained from the survey responses was analyzed using partial least squares (PLS). Results of this analysis suggest that system capability shortcomings, limited availability of system support, and low levels of technical integration were key determinants of increased intentions to replace an existing system. Notably, investments in existing systems did not appear to significantly undermine organizational replacement intentions despite support for this possibility from both theory and our semi-structured interviews.